Let's face it, there's no better time to be single than the onset of summer. And now that the sun is here to stay (at least for the next few months), your chances of flirtation and flings have just skyrocketed. Of course, there's never an appropriate time or place for such dirty deeds as smashing delicate hearts, but there are certainly a few spots that can help.
Turn in your overdue relationship at Harold Washington Library
Worried that things might get a little ugly during the break-up? You'll both have no choice but to end things peacefully and quietly at the Library, lest you invite the wrath of an overworked librarian. Once it's all over, your former mate can wallow in the self-help section or escape your insensitivity with the latest fiction.
Dance it off at Debonair Social Club
If you know for certain there's going to be tears and treacherous screams, hike it over to Debonair Social Club. The Wicker Park dance club is nearly always packed and loud enough for your forlorn lover to throw a fit (let's just hope that's the only thing she decides to throw) without causing too much of a scene.
Send mixed signals at Cafe Iberico
The relationship has been great and part of you is still invested, but you're just not ready to fully commit—especially since you're about to take a two-week vacation to the tropics. Let him down gently and thoughtfully at this downtown restaurant, where the Spanish-inspired plates are meant for sharing. The communal dining experience will indicate that you still want to leave the door open (OK, maybe just unlocked), but that you need some time (say, about three sunny months) to do your own thing.
Put in your resignation at Starbucks
Take your pick, they're a dime a dozen—not to mention predictable and costly, just like your current relationship. The international chain's impersonal atmosphere, idyllic for informal business meetings, will allow you to lay it all out on the table in a diplomatic manner. Play it safe before you give your big speech by urging your mate to order something cool and refreshing (no need for both of you to get burned). You'll also be doing your part to boost business for local places like Dollop and Cafe Avanti, as your ex is likely to steer clear of Starbucks afterward.
Mask the tears at Edgewater Lounge
Take advantage of the spacious outdoor patio at this neighborhood pub, where your soon-to-be ex won't have to feel awkward when she masks the tears with a stylish pair of shades. You'll both be able to numb the pain with another round before parting ways.
Make a quick escape at Summer Noodles & Rice
This Thai restaurant's casual atmosphere and close proximity to the Granville Red Line stop makes it the perfect spot to split ways after splitting the bill. The roar of the train during dinner will serve as the perfect soundtrack for the abrupt end to your relationship, and the spicy entrees won't make it too hard to fake tears if you need to. Just be sure to board separate cars if you're both taking the train home afterward.
Find an instant rebound at Oak Street Beachstro
If your sole intent in ending the relationship is in the spirit of summer flings, this is the perfect place to—pardon the cliche—kill two birds with one stone. Once you and your former flame have both had your share of seafood, sadness and sangria at this lakefront restaurant, you can spend the rest of your day scoping out the beach-ready crowd.
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